Missing Moments
by jane.cartier
Summary: A short collection of moments I felt should have been in the show b/w Dan and Blair. First chapter spans the first three seasons. The second chapter will take place in the 4th season.
1. Chapter 1

**Missing Moments**

He knew he wasn't dreaming. If he was, it wouldn't be something as ridiculous as this. He couldn't believe it. His father was right, not that he would ever admit it to him. There was something in Blair Waldorf that made her act the way she did. There was a reason for her biting sarcasm, superior eyes, and the emotional wall comparable to the Great Wall of China. For all her attempts at class supremacy she was a little girl at her core sitting on a dirty floor at the end of a hallway and he had just had a meaningful conversation with that person inside. After hearing her talk about her mother and meeting her briefly on the roof, he understood. Only a mother that was as calculating as Eleanor Waldorf could create the inferiority complex within her perfectionist of a daughter. He still couldn't believe that he had found common ground with _Blair Waldorf _of all people. She wasn't very different from him. He spent the entire summer thinking about how his mother had abandoned him for her art and Blair's mother abandoned her for another girl. He wondered for a moment which was worse. Sure he was upset that his mother left but he could at least rationalize that. His mother had spent her entire adult life taking care of him and Jenny on her own so that his father could live out his musical dreams on tour and now she wanted her husband to return the favor. But how do you rationalize choosing another girl over your daughter? His mother left him to do something for herself. Wouldn't it have been worse if she left him to be a mother to someone who wasn't actually her son? He had a sneaking suspicion that hers might be worse than his.

She had calmed down a little and looked less like a porcelain doll that was made to burst into tears and so he decided to take this chance to try to make friends with her. Having Serena van der Woodsen's best friend on his side might help his chances with his blonde dream girl.

"So, you think we can call a truce?"

She focused her eyes on him in that razor-sharp way that was all her own. She narrowed her eyes at him as if sizing him up before replying, "I suppose a cease fire could be negotiated."

He decided to talk in her language and continued with their Art of War like conversation, "Terms?"

"I get Serena for holidays, birthdays, and emergency shopping trips. Your terms?"

"No more sniping?" he asked weakly, feeling out of his depth.

"No deal."

He had to refrain from rolling his eyes at her, "fine, then we cut down on the biting remarks, and when I say we, I mean you, you can't badmouth me to Serena to try and break us up, and Cedric is off limits."

She looked like she may have almost been impressed but that look melted off her face quickly.

"Those are pretty hefty terms, I'll have to think about it."

He chuckled slightly at her. He should have known that a girl like her wouldn't just give in. He got up off the floor and dusted himself off and offered a hand to her. She glanced at it contemplating whether or not she would contract a communicable disease if she touched him. In the end she told him to go ahead without her. He dropped his hand, slightly disappointed, and turned to walk away.

**~ I think we can agree to those terms but you can't wear those shoes or that hair. – Blair Waldorf to Dan Humphrey in 1x04**

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"You have to decide what's important to you, keeping your pride and getting nothing, or taking a risk and maybe, maybe, having everything."

She was looking up at him from under dark lashes. Uncertainty was in her eyes and it bored into his trying to make a decision. Trying to decide whether it was worth it to take a risk on Chuck Bass. Then suddenly she gave him half a nervous smile before she spoke.

"Isn't there a third option where I could keep my pride and still get everything?" she asked him with a hopeful smile.

He just laughed and shook his head.

"Not that I know of," which causes her to huff in mock annoyance.

While she goes back into her pensive state, he examines her. She's all bright eyed, focused on her decision making, and looks almost sullen. Yet she carries sullen in the possibly the most beautiful way he'd ever seen. It makes him almost want to invent a way for her to have both her pride and everything else. Someone should really tell her that innocent vulnerability looks better on her than her Queen B attitude. Not him of course, someone else…

**~ I mean, she's not that bad… - Dan Humphrey to Vanessa about Blair Waldorf. **

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As he walked away from the train wreck that was Chuck Bass and Blair Waldorf, he felt a little uneasy. He was tuning out the incessant questions that Serena seemed to be asking him. His dad and Lily would take care Jenny, he knew that. But as he walked away he thought that maybe someone should have stayed behind to make sure Blair walked away unscathed from Chuck Bass. But his hatred for Chuck and her misplaced venom towards Jenny kept him from turning around walking back towards the scene.

He couldn't get the look of both girls' out his head. He had never seen his sister so broken. Add to that the pound of dark eye makeup that was smudged because of her tears and messy blond hair that seemed completely disarrayed despite being tied back, and she looked nothing short of a disaster to him. He was sure this only mirrored the state that her heart was in.

He had seen Blair angry before, she was all confidence, evil, and brimming with schemes. But the venom she had towards Jenny was a new one for him. He had never seen her look so mutinous, not even when she was ratting out her best friend's little tryst with her boyfriend at a Bass hosted brunch three years ago. She meant business, Jenny was not going to be allowed to stay in the Upper East Side, he was sure of it. But then unbidden, the shattered look of hurt on her face when he told her to lay off Jenny came to mind. Suddenly the two girls didn't seem different at all. They both seemed just as broken as the other. Jenny's parents were taking care of her. Who was taking care of Blair?

He almost turned back around, he even stopped mid-step, but did not turn around in the end. What he heard made him confident that he did not need to turn around. He heard Blair scream at Chuck in anger, no doubt giving him what he deserved.

"_No, don't say her name! Or anything else to me, ever again!" _

There was hurt in her voice, sure, but there was also anger, confidence, and self assurance and he realized she didn't need him to take of her. She can take care of herself. So he kept walking and finally began to fill Serena in on the details.

**~ I would barely be exaggerating if I said that Medusa wants her withering glare back. – Dan Humphrey about Blair Waldorf to his father in 1x04. **

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He was smirking at her in the most devilish way she had ever seen him look. The deviousness looked good on him, made him look sexy…almost. She thanked whatever higher power existed that Humphrey couldn't tell what she was thinking. At least she was pretty sure that he couldn't tell what she was thinking. There were moments between the two of them when she wasn't really sure of this. While she stood there entranced by his smirk, he spoke.

"Do you want to stay a while to plan?"

"Sure, I'll have a cup of earl grey," Blair ordered like she was at Starbucks.

"Uhh, okay."

She took a seat on one of the stools at the breakfast bar while set the kettle on the stove.

"You know, we could have avoided this if you believed Serena to begin with," he began suddenly.

"Believed Serena about what?"

He tilted his head to the side and gave her a look that said she knew exactly what he was talking about before telling her, "when she said she didn't overdose. We should have believed her to begin with."

She scoffed at him incredulously. The frustration and stress of the day was finally oozing itself from her every pore. Her worry for Serena, the looming media attention on Serena's overdose, Chuck's unwillingness to be there for her when she needed him, Juliet missing nowhere to be found, and now, Humphrey's self righteous indignation at the audacity of anyone who did not immediately take whatever her blond bombshell of a friend said as an irrefutable fact like he did were all too much for her. She was upset and it was about to steamroll right out of her all over Humphrey.

"Where do you get off?"

"Huh?" he seemed to be taken aback by her sudden injection of spite.

"You know, the Serena that you idolize is not the same Serena that me and Nate grew up with."

"Are you trying to say that I don't really know Serena?"

"No, I am saying that the person you know was the rebooted version who crashed today."

"Are you comparing your best friend to a computer software program?"

"I'm not joking with you Humphrey. You've never had to deal with Serena like this before. You didn't know her before she went away to boarding school. You never cleaned her vomit off your bathroom floor. You've never had to call Nate three o'clock in the morning so he can sneak out of his house and pick her up from whatever trashy bar she landed herself in that night. You didn't have to try and sober her up before first period so that she didn't miss school. You didn't have to lie to Lily and say you were having a sleep over when she called because Serena hadn't come home that night. You never had to trail after her in clubs on Saturday nights to make sure some forty year old pervert from Wall Street didn't take advantage of her only to have to watch her walk away with a twenty-five year old version of the same man. You _never _had to actually take care of her. It's not a joke. So you'll excuse me if I didn't want to take your advice of letting her run rampant and continue to try and kill herself."

She got more breathless with each passing sentence and became more frantic as well. Dan on the other hand became more shocked with each passing sentence and felt himself shrink in his spot in the kitchen. Her words shocked him. He had never thought that his blond dream girl wasn't always as he had known her, sunny, smiling, and free spirited. Everything that was right with the world. She was right, he never did any of that stuff for Serena and couldn't imagine doing it either.

They both stood there staring at each other. Each waiting for the other to make the first move. She made it.

"Look, it's been a long day. Neither of us have the energy to plot a take-down at this time of night. Why don't we just meet tomorrow morning and start fresh?"

"Sure," he managed to croak out.

"Okay, tomorrow morning at nine o'clock at the coffee shop across the street from the Ostroff Center. Don't be late."

And with that she walked out of his loft leaving him stunned. He barely slept that night. He kept tossing and turning just replaying everything she had said to him over and over in his head. Mostly he couldn't stop thinking about her and how violently she had reacted.

The brunette that had unraveled in front of him reminded him of the hurricane of a girl that laid a tirade onto Serena four years ago in that stairwell. At the time he hadn't really felt sorry for Serena as she received the verbal lashing from her best friend. She had stood him up and he wasn't really sorry to hear her best friend ram into her about butting in on her spotlight which was cutting in on his date. But he felt sorry for Serena now. He felt sorry for Serena because he now understood what it felt like to be on the receiving end of Blair Waldorf's sharp tongue, righteous indignation, and childlike vulnerability. He now understood why the free spirited girl who didn't care what people thought of her stood frozen in that stairwell and let this tiny brunette yell at her. There was nothing else for it. There was no winning against those dark eyes.

He spent all night thinking of how those sharp eyes focused on him, piercing through his mind conveying strength but also a great amount of helplessness simultaneously. It was enough to stun anyone. There was some tragic poetry written in the way her eyebrows had scrunched together in frustration. She seemed so affected by those things she listed that even if he had a rebuttal he would never have been able to voice it. There was something that broke in an indeterminable place inside him as he had watched her perfectly painted lips form harsh words and he almost made a move to touch her as he saw her lips quiver but he had managed to control himself. His comfort would not have been appreciated and he knew it. Her eyes, her expression, the words coming out of her mouth all indicated that this girl had had to do things she should not have been made to do. It made her seem older than her years. The only thing that indicated her innocence was her perfectly porcelain skin. It was flushed, radiant, and the only evidence of her youth.

When it was finally seven o'clock in the morning and he could give up the pretense of trying to sleep he rolled out of bed and got ready to meet Blair at the coffee shop. He arrived early and ordered his usual coffee and the earl grey she never got to drink last night and sat to wait for her. When she arrived she raised her eyebrows slightly as if surprised that he arrived before her. He wordlessly held out the cup of tea hoping she would take it. She did, and gave him a small smile for his trouble. They both walked out of the coffee shop and started re-hashing the events that had landed Serena at the Ostroff Center. He took his cue from her and pretended that last night had not happened and both strolled with their beverages in hand trying unusually hard to be civil to each other.

**~ Small yet giant, young yet adult, girlish yet macho. – Dan Humphrey about Clair Carlyle. **

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**A/N: Needed to get this out of my system. No doubt I have pissed off a couple readers by writing this instead of the next chapter to three words, eight letters, but I swear I am working on it. **


	2. Chapter 2

**Missing Moments 2**

It was probably the oddest Thanksgiving of Blair's life. None of her parents were there for dinner. With Nate waiting on his soon-to-be-released ex-con father, Serena not speaking to her mother, and Chuck being Chuck, there were no parents present at the dinner; an oddity, since the day is supposed to be about family. But in a way, her friends had been more her family than her actual family at certain points in her life. This was the first Thanksgiving since her father left her mother for Roman that she had actually helped in the preparation of the meal. After her father left, Blair couldn't bear to make Thanksgiving dinner without him and her mother could not bear the memories when she stepped into the kitchen. So for the past five years the Waldorfs had taken to catering their Thanksgiving meal. To top off the oddest Thanksgiving of her life, she had spent almost the entire day with _Dan Humphrey. _After rescuing Serena just in time for her to make a big show for her mother, Humphrey insisted that they have Thanksgiving together instead of just eating out. He also insisted that they split the duties which Blair considered incredibly stupid since it ended up saddling both Dan and her with most of the work, much like the mission they had been on earlier.

So Dan volunteered to go shopping, Chuck sat around making sarcastic comments about middle class living and the lack of hookers available in the city during the holiday season, Nate just sat around, Serena set the table as she claimed that it was her assigned chore in the Humphrey Thanksgiving dinner, and Blair waited for Dan to get back with the groceries so she could do the cooking. Although she loathed to admit it, she was excited to be using her dad's recipes again after such a long time.

She had hurried through the preparation of the turkey and the side dishes by happily bossing Humphrey around so that she could get to her favorite part: her dad's pumpkin pie. She went almost with childlike excitement towards the last shopping bag with the ingredients for her dad's pie. But she was disappointed once she opened it because instead of ingredients for a pie she found a pie. Pre-made, from a bakery. Humphrey had been so helpful with the food and if it was someone else she would almost say she enjoyed herself throughout the preparation. Which is why when she turned around she was only slightly biting and venomous. She gritted her teeth and asked, "what is this," brandishing the pie under his nose. She waited for his answer while Dan backed away slightly to properly examine what was being shoved in his face. He looked at her sardonically before replying, "it's a pie Blair," before going back to check on the turkey.

"I know what it is Humphrey. I am asking why it is here instead of the ingredients for an actual pie."

"It is an actual pie. We're pressed for time and I thought it'd be easier to just buy one instead of failing to make one. Besides I hate having to make them from scratch."

Blair took a deep breath and tried not to explode all over Humphrey. Although it felt like he had just sucked the fun out of this whole day with his laziness, she bit back her spite and said, "I have never met someone so uncouth and unrefined in my life. Although I guess I shouldn't expect something more from someone raised in Brooklyn."

He laughed slightly before turning to listen to the rest of her rant.

"You are going back to the supermarket and you are going to buy the exact ingredients I write down so I can make homemade pie."

"No I'm not, because we already have a perfectly good pie sitting right there."

"Yeah, plucked from some indiscriminate bakery made by some seven dollar an hour baker from a recipe found on google."

"I'm not traipsing all over Manhattan on Thanksgiving just because you have the urge to make pie."

"Yes you are."

"Really?"

"Yes, really."

"And why is that exactly."

"Because if you don't, we won't have dessert."

"We have dessert, you're holding it in your hands."

Dan could have never predicted what happened next, although he probably should have. Blair very calmly walked herself over to the wastebasket in the kitchen, pressed the lever to lift the lid and dumped said pie into it. Then she just as calmly walked over to a drawer and got a pen and paper and wrote down everything she needed and waved it front of his face until he took it. He wanted to say something. Call her a name perhaps. Something like controlling psychopath or raving lunatic but one look at her saccharine smile convinced him the fight wasn't worth picking and that she would also win. So he took the offered piece of paper, collected his coat, and went out into the city to look for the ingredients that Blair needed.

When he came back with grocery bags in hand she actually rushed to take them out his hands with an exclamation of, "finally!" After which she supervised him in the proper preparation of her dad's famous pumpkin pie. He was both surprised and taken aback, who would've known that Blair Waldorf was fond of something as commonplace as baking?

**~ It's a Blair thing, I find it's best to pick my battles. – Dan Humphrey to Rufus Humphrey about Blair Waldorf**

Dan woke from his sleep because he could no longer ignore the discomfort of his left arm. He tried to shift it but it wouldn't move. He cracked open his eyes and what he saw puzzled him and surprised him at the same time. He held his breath for a few seconds before he acknowledged what was happening. Blair Waldorf was pressed against him sleeping peacefully. Ever since he and Blair had started spending time together there had been surprises at every corner. No one had ever kept him on his toes like Blair Waldorf did. So by now, he was getting used being constantly caught off his guard with her. Sort of…

She looked so calm and still. This girl was wildly different from the girl he spent the entirety of the day practically stalking. That girl was high-powered, hell bent on control, sleep deprived, and verging on manic. She was like one of those energizer bunnies that just kept going. Except the energizer bunny didn't snipe at you and was not ungrateful when you offered help.

But this girl, this girl was calm, peaceful and relaxed. In fact, Dan didn't know if he had ever seen her so relaxed. She looked almost innocent and harmless as she slept. But Dan knew better by now.

The position she was in could not have been comfortable. Her legs were folded awkwardly underneath her, one of her arms was squished underneath his, and he was sure she would have a crick in her neck when she woke. So as much as he did not want to, he shook her gently awake.

"Mmm. Stop it Humphrey, this is the best sleep I've gotten all week and you're ruining it."

"I know, I'm sorry. I just wanted to ask if you want to take my bed so you'll be more comfortable." The only answer he got was her snuggling closer to him. This is not what he had in mind when he asked her to get more comfortable. In fact, this was probably more uncomfortable for him. He could now feel her hot breath on his neck and the warmth of her body through their clothes. Not to mention, he was now inhaling her scent with every breath he took, no doubt some fancy Parisian perfume that was intoxicating. He tried to stay extremely still, trying not to disturb her or draw attention to his current state of mind. She sighed softly and Dan berated himself for finding it adorable before she said, "Dan."

"Yes," he said, almost holding his breath.

"I'm sorry I used you as my drug mule."

He almost laughed because Blair Waldorf just apologized to him. No doubt she would deny it in the morning. For all her adamant declarations that they were not friends, he had never felt that she was more his friend than this moment. After all, this is what you do in friendships, right? You apologize when you're wrong, watch movies, eat pizza, and…fall asleep pressed against each other? He stopped thinking there. It was probably better not to examine this further. Instead, he slowly extracted himself from under Blair, laid her down properly on the sofa and covered her with the quilt laying on the couch.

The next morning they took plausible deniability and pretended nothing out of the ordinary had happened last night. He did not prod her about apologizing to him in her sleep and she did not ask why he left her there on the couch alone. They ate breakfast together and made plans to meet up later that day to finally go see the Degas exhibit.

**~ Paris is complicated and beautiful, much like you. – Prince Louis Grimaldi about Blair Waldorf. **

She ran as quickly as she could into her room and slammed the door shut leaning her forehead against it taking deep breaths to calm herself. She couldn't believe what had just happened. She couldn't believe what she had just done. She had kissed him. She, Blair Waldorf, had kissed lonely boy Dan Humphrey. Then she left him standing there and ran up to her room. She could hardly let the voice in her head speak what she thought just in case someone could hear her thoughts. Just in case he could hear her thoughts. The last few weeks had only encouraged her to believe that he could hear her deepest, darkest thoughts. With a moment or two more of trepidation she admitted to herself what she couldn't admit downstairs. And that was that their kiss had left her breathless. She admitted that it had felt exhilarating to finally act on the desire she had had since he let her order whatever takeout she wanted, let her choose the movie they watched, and let her fall asleep on his strong shoulder. She admitted this wasn't the first time she'd thought about kissing him. There were more times than she'd like to count and now that she'd finally done it she couldn't remember why they hadn't been doing this all along. She couldn't fathom at all why they spent late nights talking and instead of melded together at the lips on his couch. It was safe for even Blair to assume that she had liked kissing Humphrey, even with his bad taste in clothing. Although he did look passable tonight. Except for the fact that he could have used a good tie. She supposed with some helpful direction from her his fashion sense could improve.

She stepped away from her door and began pacing the length of her room repeatedly with a nervous and excited energy that she hadn't felt it some time. She hadn't felt like this in a long time. She hadn't felt like this since she thought Nate was going to come to her birthday party and give her a diamond necklace and tell her that he loves her. No, she hadn't felt this excited since she was waiting for Chuck to whisk her away to Tuscany after Bart and Lily's wedding. No, she hadn't felt this excited since she ran into the Empire late in meeting Chuck hoping to convince him to give her another chance. No, she'd never felt this excited at all. All those times had always ended in heartache. But this, this was different. This was Dan Humphrey. When that had become something that made her want to trust him and not loath him, Blair didn't know. All that she knew he wouldn't do to her what the others had. He wouldn't hurt her. Her thoughts were running a mile a minute. So much so that she was having trouble keeping up.

_What should they do now? _

_I felt something. I don't know what it is. I can't put a name to it because I'd never felt this way before._

_He obviously had to have felt something. If he hadn't he wouldn't have showed up here asking to kiss me. _

_Of course Humphrey would go the Prince Charming route and ask for a kiss. _

_That was beside the point. _

_What now? _

_We both felt something. _

_But I can't imagine sleeping with Humphrey just yet. _

_Okay, maybe I could imagine it but that doesn't meant that we were there yet. _

_The most they'd done before the kiss was fall asleep with each other._

She stopped abruptly and stood idly in the middle of her room when the thought occurred to her. She remembered an offer made to her by another hipster she had met at a loft party. She had called him Columbia and he had offered to take her on a date.

_A date. _

_Her and Humphrey could go on a date. _

_Granted I had only been on a couple of dates with someone I wasn't already seeing seriously. But still. _

_We could go on a date. _

_It could be fun. Although she loathed to admit it to another human being, I enjoyed spending time with Humphrey. _

_We could keep doing what we had been doing. _

_We could go see a movie or an art exhibit. _

_But maybe this time he'd come to the apartment instead of meeting me at a predetermined destination disguised in some strange place. _

_Maybe this time he could put actual thought into his wardrobe and compliment me on mine. _

_Maybe this time he'd try to hold my hand while they watched a movie. _

_Maybe this time our flirting over dinner would be intentional. _

_Maybe this time he'd walk me to my door and kiss me goodnight. _

A broad smile spread involuntarily across her face at the mere thought. She was almost bouncing on the balls of her feet before she almost jumped out of her skin at a very loud sound. There was a loud banging sound on her door accompanied by a very unexpected voice.

"Blair, Blair it's me Chuck. Let me in. I need to talk to you!"

Blair's heart froze as it was doused in the cold water of harsh reality. Chuck. In all her lofty plans she had forgotten entirely about Chuck and now he was back at the front of her thoughts with full force. She had forgotten. She had forgotten she loved Chuck.

"Go away Chuck!"

"I need to talk to you Blair! Please!"

"No! It's late and I'm tired. I don't want to see you. Leave or I'll call Dorota!"

Chuck always was a little frightened on Dorota so he ceased trying to beat down her door and left her alone. She only sighed with relief when she heard the ping of the elevator. She sat heavily on her bed and continued to let her newest revelation dawn on her. She had forgotten. She had forgotten she was in love with Chuck. She had promised that they would be together. She still remembered how he had so sadly promised her that two people who were meant to be together would find their way back to each other. She had believed those words then and she believed them now. Chuck was her destiny. He always had been. So why should she delay the inevitable?

_Yes, spending time with Humphrey had been great. _

_They always had things to talk about even if it was the most inane things. But even when they didn't talk it was comfortable. _

_His taste in movies could use some improvement which I had most definitely made. _

_But the quality of his Netflix cue far surpassed my own, that I'm not ashamed to admit. _

_And he wasn't bad to look at. Although his taste in art was more abstract than I'd like. _

_Despite his plaid shirts and those t-shirts that made him look homeless, he was almost handsome. _

_And I felt this nervous fluttering thing in my stomach whenever he looked at me in that teasing sort of way. _

_But all that was moot point because Chuck was my destiny. There was no use in having a frivolous rendezvous with Humphrey when Chuck was meant to be the Prince Charles to my Princess Diana. _

_Besides, Humphrey was meant to be with Serena. They belonged together. He'd always loved her. No matter who he'd dated after, he always chose Serena in the end. It was stupid of me to think that he wouldn't do the same to me. _

_He and Serena were perfect together. She was golden and he idolized her. _

_Even though Serena would never be able to keep up with Dan at an art exhibit like I could. And he and Serena could never debate like they could. But that doesn't matter. _

_They should both stop trying to run from the life they were meant to have. She should stop avoiding her future and embrace it and go back to Chuck and he should. . .do what he wants. He could go back to Serena if he wanted. _

_Yes, that's it. _

_She was going to go back to Chuck. _

_She looked dejectedly at her door where Chuck had been pounding moments ago. _

_It was late. _

_Reunions could wait. _

_She climbed into bed, put on her sleeping mask, and pulled her duvet over her head. _

_She'd deal with Chuck tomorrow. . . if she felt up to it. _

**~ She just walked away, stunned and left me standing in her foyer. – Dan Humphrey about Blair Waldorf's reaction to their first kiss.**


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